Acetyl chloride → HCID 4835210, compound

HRID 1856926Notes

Reaction equation

HRID 1856926 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6](=[O:19])[C:7](=[CH:9][C:10]3[CH:18]=[CH:17][C:16]4[O:15][CH2:14][O:13][C:12]=4[CH:11]=3)[O:8][C:4]=2[CH:3]=1.[C:22](Cl)(=[O:24])[CH3:23].C(OCC)(=O)C>N1C=CC=CC=1>[C:22]([O:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6](=[O:19])[C:7](=[CH:9][C:10]3[CH:18]=[CH:17][C:16]4[O:15][CH2:14][O:13][C:12]=4[CH:11]=3)[O:8][C:4]=2[CH:3]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 4834830HCID 4834830, compound

Product 1

HCID 4835210HCID 4835210, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

After 6-hydroxy-2-piperonylidene-3(2H)-benzofuranone 0.5 g was dissolved in pyridine 5 ml, acetyl chloride 0.2 ml was added, and the mixture was refluxed for two hours. The reaction mixture was cooled to room temperature, ethyl acetate 50 ml was added, and the mixture was washed with 2N-hydrochloric acid 50 ml twice. After the ethyl acetate solution was dehydrated with anhydrous magnesium sulfate, it was concentrated under reduced pressure. The crude extract was fractionated by silica gel column chromatography (silica gel: 50 g, eluted with solvent 500 ml of hexane:ethyl acetate=1:1) and the fraction was concentrated to dryness at a temperature of 40° C. under reduced pressure to obtain crystals. The crystals were filtered and dried on phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure to obtain the desired compound 539.5 mg.

Workup

  1. temperaturethe mixture was refluxed for two hours
  2. washthe mixture was washed with 2N-hydrochloric acid 50 ml twice
  3. concentrationwas concentrated under reduced pressure
  4. extractionThe crude extract
  5. washwas fractionated by silica gel column chromatography (silica gel: 50 g, eluted with solvent 500 ml of hexane:ethyl acetate=1:1)
  6. concentrationthe fraction was concentrated to dryness at a temperature of 40° C. under reduced pressure
  7. customto obtain crystals
  8. filtrationThe crystals were filtered
  9. customdried on phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure

Sources & evidence

ORD record
ord-386a65940d344fe3a38cd4bf37ada1d1
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

Loading…